Page 23 of 26
The Journal of Organic Chemistry
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126.0 (q, J = 3.7 Hz), 125.1, 124.9, 122.4, 120.8, 120.1, 117.5, 112.3, 109.3, 49.8, 30.8, 19.5. HR-MS (ESI-
TOF) m/z: [M+Na]+ calcd for [C22H14F3NNaO4]+ 436.0767; Found 436.0765.
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1-(7-methoxy-4-oxo-2-phenyl-4H-furo[3,2-c]chromen-3-yl)pyrrolidin-2-one (7g): White solid; (64 mg,
75%); mp 190-193˚C. IR (MIR-ATR, 4000–600 cm-1) νmax = 3061, 2934, 2846, 1735, 1633, 1603, 1495,
1460, 1408, 1372, 1330, 1256, 1198, 1160, 1121, 1027, 969, 946, 838, 766, 693, 634, 570; 1H NMR (400
MHz, CDCl3): δ 7.83 (d, J = 8.3 Hz, 1H), 7.79 - 7.74 (m, 2H), 7.50 - 7.44 (m, 2 H), 7.42 - 7.36 (m, 1H),
6.99 - 6.92 (m, 2H), 3.89 (s, 3H), 3.89 - 3.70 (m, 2H), 2.71 - 2.61 (m, 2 H), 2.32 (t, J = 7.6 Hz, 2H);
13C{1H}NMR (100 MHz, CDCl3): δ 176.5, 162.3, 157.1, 156.8, 154.6, 149.9, 129.2, 129.0, 128.3, 125.3,
121.7, 118.0, 113.1, 106.8, 106.0, 101.4, 55.8, 49.8, 30.9, 19.4. HR-MS (ESI-TOF) m/z: [M+H]+ calcd for
[C22H18NO5]+ 376.1179; Found 376.1178.
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1-(2-(4-fluoro-3-methylphenyl)-7-methoxy-4-oxo-4H-furo[3,2-c]chromen-3-yl)pyrrolidin-2one
(7h):
white solid; (78 mg, 86%); mp 204-207˚C. IR (MIR-ATR, 4000–600 cm-1) νmax = 3633, 2933, 2886, 1734,
1699, 1635, 1608, 1503, 1460, 1420, 1337, 1249, 1161, 1114, 1026, 973, 945, 835, 766, 720, 696, 623,
552; 1H NMR (400 MHz, CDCl3):δ 7.82 (d, J = 8.8 Hz, 1H), 7.59 (dd, J = 1.5, 7.3 Hz, 1H), 7.57 - 7.50 (m,
1H), 7.08 (t, J = 8.8 Hz, 1H), 6.98 - 6.91 (m, 2H), 3.89 (s, 3H), 3.88 - 3.79 (m, 2H), 2.74 - 2.49 (m, 2H),
2.34 (d, J = 1.5 Hz, 3H), 2.33 - 2.26 (m, 2H); 13C{1H}NMR (100 MHz, CDCl3): δ 176.4, 162.9, 161.38 (d,
J = 248 Hz) 157.1, 156.6, 154.6, 149.4, 128.7 (d, J = 5 Hz), 125.8, 125.7, 124.8 (d, J = 8 Hz), 124.3 (d, J =
3 Hz), 121.2, 117.5, 115.9 (d, J = 23 Hz), 113.1, 106.8, 105.9, 101.4, 55.8, 49.8, 30.9, 19.4, 14.8, 14.7. HR-
MS (ESI-TOF) m/z: [M+H]+ calcd for [C23H19FNO5]+ 408.1242; Found 408.1247.
1-(1-hydroxy-2-oxo-2-phenylethyl)pyrrolidin-2-one (A): White solid; (78 mg, 96%); mp 98-101˚C. IR
(MIR-ATR, 4000–600 cm-1) νmax = 3225, 3074, 2959, 2883, 1692, 1668, 1594, 1491, 1417, 1352, 1265,
1233, 1177, 1116, 1024, 1000, 963, 850, 798, 756, 683, 616, 567, 535; 1H NMR (400 MHz, CDCl3):δ 8.13
- 8.05 (m, 2H), 7.69 - 7.62 (m, 1H), 7.55 - 7.47 (m, 2H), 6.69 (d, J = 6.8 Hz, 1H), 4.69 (d, J = 6.8 Hz, 1H),
3.48 (dt, J = 6.1, 8.9 Hz, 1H), 2.86 (dt, J = 5.1, 8.9 Hz, 1H), 2.45 (ddd, J = 7.1, 9.7, 17.0 Hz, 1H), 2.39 -
2.26 (m, 1H), 2.08 - 1.95 (m, 1H), 1.92 - 1.78 (m, 1H); 13C{1H}NMR (100 MHz, CDCl3): δ 195.9, 175.4,
135.0, 131.9, 129.1, 129.0, 77.4, 77.1, 76.7, 73.3, 41.3, 30.9, 17.8. HR-MS (ESI-TOF) m/z: [M+ H]+ calcd
for [C12H14NO3]+ 220.0968; Found 220.0969.
1-(2-oxo-1,2-diphenylethyl)pyrrolidin-2-one (C): White solid; (64 mg, 95%); mp 104-106˚C. IR (MIR-
ATR, 4000–600 cm-1) νmax = 3747, 3689, 3673, 3649, 3614, 3565, 3061, 2978, 2891, 1676, 1596, 1579,
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1520, 1450, 1416, 1362, 1268, 1206, 1100, 1076, 1030, 934, 854, 794, 762, 743, 697, 635, 590, 555; H
NMR (400 MHz, CDCl3):δ 7.96 - 7.87 (m, 2 H), 7.52 - 7.45 (m, 1 H), 7.41 - 7.31 (m, 5 H), 7.30 - 7.24 (m,
2 H), 6.84 (s, 1 H), 3.81 (dt, J = 5.9, 8.8 Hz, 1 H), 2.92 (dt, J = 5.4, 9.0 Hz, 1 H), 2.57 - 2.36 (m, 2 H), 2.16
- 2.03 (m, 1 H), 1.97 - 1.83 (m, 1 H); 13C{1H}NMR (100 MHz, CDCl3): δ 196.5, 175.2, 135.0, 134.5, 133.4,
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